Pyridine → HCID 19165311, Verbindung

HRID 963019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963019
[CH:1]1[C:13]2[CH:12]([C:14]([OH:16])=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C.O>[C:24]1([CH2:23][NH:30][C:14]([CH:12]2[C:13]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)=[O:16])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

9

Edukt 4

HCID 1049PyridineHCID 7504BenzylamineHCID 65578Oxalyl chlorideHCID 748099-Carboxyfluorene

Produkt 1

HCID 19165311HCID 19165311, VerbindungAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 9-fluorene carboxylic acid (2.10 g, 10.0 mmol) in 50 mL of CH2Cl2 was treated with oxalyl chloride in dichloromethane (6.0 mL, 12.0 mmol) and two drops of DMF. After 0.75 h, the mixture was concentrated under reduced pressure to give a white solid. The solid was diluted with 50 mL of CH2Cl2, cooled to 0° C., treated with benzylamine (1.17 g, 11.0 mmol) and pyridine (0.87 g, 11 mmol). The transparent yellow solution was stirred for 3 h at room temperature and diluted with ethyl acetate and water. The organic fraction was dried over Na2SO4 and concentrated to a white solid. The solid purified by trituration with hexanes and recrystalization from hot methanol to give 2.60 g (86%) of title compound as white flakes. mp 195°-200° C.

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto give a white solid
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. concentrationconcentrated to a white solid
  5. customThe solid purified by trituration with hexanes and recrystalization from hot methanol

Quellen und Nachweise

ORD-Eintrag
ord-aa8327bf931f478c9a3244afd183fd65
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760246

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